beta, beta&#39; dihydroxydiethyl cyanamide



Patented Mar. 25, 1941 UNITED STATES PATENT OFFICE 3,5 DIHYDROXYDIETHYL CYANAMIDE Maine No Drawing. Application May 23, 1939, Serial No. 275,225

1 Claim. (01. 260-551) This invention relates to a new disubstituted cyanamide compound of the formula- R-CHrCH:

/NCN 11-011mm where R is hydroxy.

This compound may be generally prepared by the reaction between the corresponding secondary amine, cyanogen chloride and caustic soda. A

preferred equation for this reaction is as follows: R-CHrCHq NHjONOl-l-NaOH 15 Rom-om R-CHz-CH:

NoN+Nao1+mo R-CHz-CH:

. Eatample 212 grams of 5,,e'-dihydroxydiethyl amine are dissolved in one liter of water. After cooling the solution to about 5 C., 123 grams of cyanogen chloride are gradually added with stirring. When this addition is completed, the mixture is agitated with a solution of grams of sodium hydroxide dissolved in 400 cc. of water and allowed to stand one hour. The aqueous solution is concentrated under vacuum to approximately 250 cc. The residue is diluted with alcohol and filtered to remove the salts. The filtrate, which is slightly alkaline, is neutralized with dilute hy- 5 drochloric acid. Benzene is added and the concentration continued. Further salt separates and is removed by filtration. The last traces of benzene and alcohol are driven out at C./30 mm. The fi,,B'-dihydroxydiethyl cyanamide re- 10 mains as a slightly yellow viscous liquid, which decomposes when an attempt is made to distill it at 250 C./1 mm.

This new compound is particularly useful as an intermediate and may be applied to the tex- 15 tile, insecticide and plasticizing arts.

While the invention has been described with reference to specific embodiments, it is to be understood that it is not to be limited thereto, but is to be construed broadly and restricted 0 solely by the scope of the claim.

We claim:

As a new compound, B,,9'-dihydroxydiethyl cyanamide.

25 INGENUIN HECHENBLEIKNER. .CHRIS BEST. 

